


Hello, Sailor.

by Winchest09



Category: Supernatural
Genre: AU, Eventual Romance, F/M, Fluff, Fluffy fic, Romance, Sailor AU, Sailor Dean, Slow Burn, Slow Romance, Smut
Language: English
Status: In-Progress
Published: 2020-10-17
Updated: 2020-11-05
Packaged: 2021-03-09 00:35:24
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 14,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27065737
Author URL: https://archiveofourown.org/users/Winchest09/pseuds/Winchest09
Summary: Y/N was never a big fan of sailors, so when a ship full of them dock at the harbor in her town, she’s anything but happy. However, there is one in particular that is determined to prove to her that not all men of the sea are the same, and dedicates each day of his shore leave to the task of changing her mind. Will the green eyed sailor prove his point, or hers?
Relationships: Dean Winchester/Reader, Dean Winchester/You
Comments: 13
Kudos: 20





	1. Chapter One.

**Author's Note:**

> Hey Everyone!
> 
> Welcome to the beginning of my brand new fiction! If you're familiar with me, then you will know that I have just finished my 30 chapter fiction, Life for Rent. 
> 
> So...time for something new! All aboard the ship for Hello, Sailor. It's gonna be a journey! 
> 
> \- Winchest09

The afternoon sun beat down over the diner patio, casual chatter echoed along the gentle breeze, as Y/N wiped down the few vacant tables that were outside. She hummed quietly to herself as she ran the wet dishcloth over the rustic wooden surface, stopping to stand for a moment, appreciating her surroundings. The back terrace was filled with small tables, little red and white umbrellas covering them to keep the customers cool. Strings of white fairy lights were entwined with vines over head, leading down into long horizontal plant pots which were filled with colorful African daisies. Y/N smiled to herself, the choice of plants being a nod towards the diners name; The Daisy Chain. 

Turning on her spot, she looked out over the docks, her eyes automatically landing on the ship that was currently mooring in the bay. The smile that she was wearing faltered somewhat, her nose curling in slight disgust at the sight. She knew that the large vessel harbored the type of men she was not all too fond of; sailors. They would come ashore shortly, filtering into the diner and taking over with their loud jeers and colorful ways. They would be eyeing up each passer by, not wasting a moment to make their move and enjoy most of the time they had while on land. It made Y/N feel nauseous. 

With a huff, she picked up her wash bowl and cloth before heading back inside, letting out a small sigh of relief when the air conditioning graced over her skin. Even though she had dressed in a white cotton blouse paired with a black polka dot flowing skirt, the heat of the summer was highly noticeable. However, she didn't mind, especially since it’s her favorite season of the year. 

Y/N made her way past some tables and opened the hatch on the counter to pass through, placing what used glasses she had collected into the dishwasher before rinsing her dirty cloth under the tap. She’d been working at The Daisy Chain for a number of years now. It was a quaint little diner just off the harbor with a fabulous view of the sea. The owners, Jody and Donna, had soon become some of her closest friends. They took Y/N under their wing, training her in all aspects of the job, and now, it was her home away from home. 

“What are you still doing here, darlin'? You should have clocked off an hour ago,” a cheery voice called, as Y/N felt a slight tap on her shoulder. Turning around, she wiped her hands dry on the nearest towel, smiling at her present company.

“You needed the help, Donna. It was busy, and no doubt, we’re about to get packed with people,” Y/N grumbled, nodding her head in the direction of the shop as she folded up the square fabric in her hand, throwing it on the side with a forcible thud. 

The blonde boss just rolled her eyes as she bustled by her to get to the serving hatch, wanting to pass over what order slips she had. She knew about Y/N’s issues with sailors, ever since the woman had begun working at the diner a few years ago. 

“You need to get yourself out there, girl. Find yourself a good man,” Donna encouraged, turning to her side and leaning against the wall, using her hand to signal the chef.

“Yeah, well, when you find a  _ good _ man, you let me know,” Y/N sighed, resting opposite her colleague. 

She watched on, as Rufus - the diner’s cook - came and took what orders Donna had and left a bowl of fresh fries in their wake. 

“Well, then maybe just a man.” Donna winked, smiling as she reached into the newly placed dish next to her. “Hey, I know. Me and Jody have decided to go out tonight. Local bar, good music. Why don’t cha join us, hmm?” she asked, filling her mouth with the delicious potato goods before sliding the bowl along the hatch to offer some to Y/N, who began to eye her suspiciously.

"And this impromptu night out has  _ absolutely _ nothing to do with the ship that’s docked today, right?" she deadpanned, before grabbing a handful of fries from the offered dish. As Y/N started to nibble on the end of one, Donna pulled the bowl back and continued to eat herself, a coy smile slowly pulling at her lips. 

“Maybe?” she shrugged, her expression morphing into a wide grin. 

“Donna!” Y/N exclaimed, a little exasperated, as she leant over to playfully slap her friend's shoulder. “The last thing I want to be is some notch on a random sailor’s bedpost. Who knows where they’ve been and who they’ve been with, not that they care,” she scoffed, wiping her hands down the front of her small white apron. 

Y/N had a point. It was common knowledge that sailors would come ashore, spend whatever nights they had in bars and willing people’s beds. They would then be gone in the morning without so much as a goodbye. She also knew that she shouldn't tar all sailors with the same brush, but at the same time, all she had ever heard about them was bad news. Her neighbor was left heartbroken when a sailor never returned her letters. A friend was inconsolable when a sailor promised her the world only to leave her with a newborn baby. She knew that she wasn’t living in olden times anymore, but the fact still remained the same, at least in her experience. 

“Look, Y/N. It’s been too long since you’ve had any kind of tussle between sheets, even if it’s just fighting for the blanket,” Donna muffled through a full mouth. “Also - and don’t shoot me for sayin’ - but when was the last time you put yourself first, sweetie?”    
  
“I have a lot of things to do, with work and my Nanna,” Y/N mumbled, shrugging her shoulders as she brought a hand to her hair. 

“And your Nanna would not want you cooped up in your house, day in and day out.” The blonde raised her eyebrows at her employee, noticing how she didn’t disagree with her. “You need to let your hair down. So even if you don’t want to admire a man in uniform, at least come and have a drink with us,” she pleaded, her warm hands now resting over Y/N’s as she tried her best to convince her with a reassuring manner. 

“Fine,” she sighed, giving in to Donna’s puppy dog eyes, “but only because  _ someone _ has got to keep an eye on you both.” 

Her boss squealed a little on the spot, releasing Y/N’s hands and pinching at her cheeks. 

“Atta girl,” she praised, before grabbing what fresh completed orders had been placed into the serving hatch as they were talking. “Now go home and start picking out your outfit. I’ll swing by with Jody after we close up here, we can get ready together.”

"Alright," Y/N breathed, nodding with a warm smile on her face, as she watched her boss walk away with the plates of fresh food. 

She appreciated Donna and Jody more than she could put into words. They were like her older sisters, always calling her out on her nonsense, always knowing the exact words to say to make her smile. She knew her friend was right; it had been too long since Y/N had allowed herself any kind of fun, so maybe going out for the evening wasn’t such a bad idea. 

After undoing her apron, Y/N folded it neatly and placed it underneath the counter. She walked into the kitchen, through to the staff room where she grabbed her small purse and headed out the backdoor. It was late afternoon and as she began to walk home, her eyes fell on the ship that was moored in the harbor up ahead. She felt the disgust starting to bubble away inside her already. After what had happened to her, she would be damned if she allowed any man - let alone another sailor - break her heart again. 

Slowly walking along the pier, her shoes thudded lightly against the pavement, while she watched the fishermen sort through their catch as she passed. She enjoyed this part of the town, the smell of the salty air that sifts in with the breeze, the atmosphere of the workers she passed, each of them nodding their caps to her in greeting. Her favorite time to be here at this beautiful part of town would be dusk, when the sun was setting and created an orange hue that would bask over the gentle waters. She would sit on the beach, her toes curled in the sand and just watch how the colors changed in the sky. It was blissful. 

Taking a deep breath, Y/N’s gaze made its way back onto the large ship she was approaching, and she instinctively crossed her arms. As she got closer, she noticed how there were several sailors working in the vicinity of the vessel, some securing thick rope around the mooring posts situated on the docks. Others were just huddled together as they chatted, all dressed in the same uniform. She didn’t like to stare, not wanting to give any of the sailors an opportunity to think she was interested, but at the same time, she couldn’t look away. 

As Y/N took in the view of them just a few feet in front of her with her arms still crossed tightly across her chest, a sudden unexpected breeze from the sea blew past her, causing her hair to whip around her face and her skirt to lift slightly, showing a bit more leg than she would have liked. Automatically, Y/N unfolded her arms and grabbed at her skirt, holding it down while her cheeks burned with embarrassment. There was no way this incident would have gone unnoticed. 

Almost immediately, the group of sailors that she was walking past started whistling at her, cheering and laughing at the mishap. In that moment, she wished the ground would have just swallowed her whole. She brushed away the hair from her face with her free hand, her vision cleared and landed back on the group of sailors. She watched how they all beamed at her; still catcalling, pulling faces and making sexual jeers. All but  _ one _ . 

There he stood, one hand in his dress white pocket, the other resting at his side, as his eyes bore into her own. She noticed his chiseled jawline, how his lips were perfectly plump and held a slight smile. Y/N caught his gaze as she took a moment to smoothen down her skirt and fix her hair. She cleared her throat and straightened her posture, before she held her head high to continue on her way. She turned her body away, the sight of him the last thing she broke away from, before she carried on walking home, resisting the urge to look over her shoulder. 

Her passing by only allowed their exchange of looks to be short, but the distinct color of his irises was one she was going to remember, whether she liked it or not. Moss green with a hint of amber, which reminded her of the way the rising sun would catch the water in the bay on crisp summer mornings. The same sparkle one would see as the rays glistened in the ripples of the waves, hiding the unknown depths of the abyss. It was hypnotising, mystical and completely enchanting, just like the virtuous man who did not laugh at her blunder, just like the mysterious man who had returned her gaze. 

Just like the green eyed sailor.    



	2. Chapter Two

**Notes for the Chapter:**

> Thanks so much for the love you guys have shown already for the new series. 
> 
> Hope you enjoy chapter two ;) 
> 
> \- Winchest09 xox

Y/N walked along the edge of the docks with Donna and Jody at her side as they headed towards The Cove, the local bar and hotspot for nightlife. She smiled while listening to the excited rambling of her friends, one hand holding down the edge of her baby blue flare dress to ensure it wouldn’t blow up with the wind like earlier that day. She wanted to keep the shred of dignity she had left before she entered the club, already spotting groups of sailors huddled around the entrance as they approached.

They hadn’t even reached the front of the venue when the jeering started, wolf whistles and catcalls aimed in their direction. However, Y/N kept her focus on the red painted wooden door that she was getting closer to, ignoring the men as she paced forward, desperately wanting a strong drink to calm the nerves inside of her. It wasn’t that she was anxious about being out for the night or that she was about to step into a bar full of strangers, yet she was wary of the fact that some of the guys may have already seen a bit more than she wanted, thanks to her earlier skirt mishap. Y/N prayed it wouldn’t come back to haunt her tonight.

Thankfully, due to Jody knowing The Cove’s owner, they didn’t have to wait in the queue outside; the bouncer acknowledged them with a curt nod as he stepped aside to allow them to pass. Y/N took note of her surroundings, the dark wooden interior, warm lighting and the soft jazz music playing making her smile slightly. She took a deep breath, clutching her purse tightly in her hands before she felt two sets of warm arms wrap around each of her own. Jody and Donna were at her side, both of them wearing a grin that reached their ears as they drank up the atmosphere.

“How did I let you talk me into this?” Y/N nervously spoke under her breath as her friends dragged her forward.

“Because deep down, you know you needed a night out,” Jody told her, gently patting her hand on Y/N’s forearm.

“She’s right, sweetcheeks. You need to let loose,” Donna affirmed, a wide grin on her lips. “Neither of us are saying you need to go off with any of these men, it’s just nice to have you out instead of you being curled up on the couch with a book.”

Y/N frowned, playfully. “There's nothing wrong with reading a book!”

The blonde laughed. “Didn’t say there was, but it'll do you good to let go for once.”

With a tight squeeze of her arm, Donna released her when they reached the center of the room, looking for a vacant table that would accommodate the three of them. Y/N couldn’t help but smile at her friends’ enthusiasm, their personalities infectious.

"Could I buy you girls a drink?" A low voice sounded from behind them, causing Y/N to whip her head around fast.

Standing behind them were two sailors, both of them tall, wearing their dress white uniforms as they smiled from ear to ear. She didn’t even have to look at her friends to know what the answer would be, the excitement oozing off of them in waves.

"Sure thing, sugar," Donna agreed, her pearly white teeth biting into the corner of her glossy red lips as she took the offered outstretched arm.

"Would you like to dance?" The other sailor asked, his attention and sole focus on Jody next to her.

"Oh. Aye aye, Captain," Jody swooned, linking her arm through the waiting man’s as he led her to the dance floor.

"Jody, he's not actually…" Y/N started as she watched her friend be escorted away, "...a captain," she murmured, her words falling on deaf ears as Y/N's eyes landed on the double gold bars with a single star sewn onto his shoulder board, giving away his lieutenant status.

Pursing her lips, she looked around, taking in the undertone of the room. Groups of sailors huddled together, laughing with beverages in hand while others used the dance floor to show off their moves. She eyed Donna up one corner, her fingers holding onto the straw from her cocktail as she grinned flirtatiously up at the man who had bought it for her. Deciding she needed a drink for herself, Y/N made her way towards the long bar at the back of the venue.

She was lucky that it was quieter in this section of The Cove. A few barstools remained free as the server leisurely made his way around, waiting patrons with ease. With elegance, Y/N tucked her dress under her legs as she slid onto a seat, resting her purse on the mahogany surface in front of her as she waited to order. With her vision trained on the array of alcohol bottles that were shelved on the wall, she was unaware of the warm body that had slid into the seat next to hers.

"You look mighty fine, lady," a sailor drawled, as he ran his tongue over his teeth, drinking all of her in. "How about I buy you a drink? The name is Cole."

Y/N turned her head slightly, noticing the man with blue eyes and faded brown hair, his crisp white uniform crinkling as he casually leaned back onto the surface next to her. His eyes were already roaming, twisting the cocktail stick he held with his lips by his tongue, his eyebrows raised. She couldn't help but curl her mouth up in disgust.

"How about you don't?" she retorted. Hoping he got the message, she turned away and signaled for the barman so she could order a martini.

"Aw, come on, doll. Don't be a prude now," he continued, sliding his leaning arm along the polished wood to be closer to her.

Y/N could already feel the anger bubbling away in the pit of her stomach, venom forming on the tip of her tongue as she got herself ready to tell this sailor next to her to back off. Yet, before she could respond, her mouth already open for her counter, a third party interrupted them.

“A petty officer, second _class,_ should remember his manners,” the deep voice sounded from behind her, the gruff comment carrying over the jazz music playing, his deep tones vibrating through her. "The lady said no, Trenton. So why don't you just head on back to your buddies in the corner?"

"What? You think you got a shot?” Cole muttered under his breath, barely loud enough for her to hear. He looked from her defender before scowling back at Y/N. “Pft... This one has fearful dick syndrome," he spat, causing the woman to widen her eyes, "A fuckin’ prick tease after her little show this afternoon."

Y/N swallowed hard, her small fists tightening into balls as she tried to remain ladylike about the situation. She also felt the heat creep back into her cheeks, now that she was reminded of the earlier mishap with the wind. She was naive to think that the moment wouldn’t come back to haunt her tonight, especially considering she was surrounded by the people who had probably seen the spectacle.

"Trenton, I'd start walking if I were you.” The growling threat was followed by her protector sliding himself in between her and Cole. “Learn to have a little respect," he warned, his voice dangerously low.

After a few intense seconds, Cole pushed himself off of his stool and stalked away from them. Y/N took a deep breath to calm herself, her eyes focused on the martini that had just been placed on a napkin in front of her. Out of her peripheral vision, she saw that the man who had intervened waited until Cole was out of sight before he slowly began to turn around towards her. She angled her face slightly to the side, allowing herself to glance up partially to look upon the person who wanted to defend her, only to be greeted with the shining orbs that had captivated that afternoon.

The green eyed sailor.

Y/N reached for her martini and took a generous sip, not wanting to risk being captivated by his gaze. "You didn't have to do that. I had it under control," she remarked, slightly annoyed and embarrassed that he had become her savior.

"Any opportunity I can get to knock him down a peg or two is worth it," he responded, shaking his head. "The guy is a dick."

She raised her eyebrows slightly, surprised to hear that sentiment from another sailor. "Well... thank you, I guess, Mr?"

"Winchester. Dean Winchester," he replied, a calming yet warm smile on his features.

"Thank you, Mr. Winchester," she told him softly, her slender fingers wrapping around the glass stem of her martini glass.

"My pleasure, ma'am," he answered before motioning down to the stool Cole was previously on. "Do you mind if I sit?"

Y/N shook her head, still slightly bewildered by what had just happened. They sat in silence, one that wasn’t awkward yet it wasn’t entirely comfortable either. Y/N was waiting on him to bring up the earlier incident, the one when she had first spotted him at the docks. She was preparing herself for the comments, the teasing and the bad pick up lines and yet, none were made. Dean sat next to her quietly, lifting two fingers to signal the barman before ordering himself a whiskey. She glanced over his attire, taking his moment of distraction to study his uniform. Dean was decked out in his dress whites, his shoulder boards weaved with three gold bars and a star. That told Y/N all she needed to know about his position. He looked smart, presentable; everything he should be considering he was a Lieutenant Commander.

Taking another sip of her cocktail, Y/N slowly spun her stool around to look out across the rest of The Cove. She had to admit that she was enjoying the atmosphere, her heel covered feet tapping slightly to the beat against her seat, while she tried to spy her friends through the ever growing crowd. Jody and Donna were both dancing with their chosen sailors, wide grins on their faces as they threw their heads back with laughter. They were having a good time which in turn, made Y/N smile too.

It was then that they caught her eye, both of them using their looks and expressions to communicate to Y/N, imploring her to get closer to the handsome Lt. Commander next to her, which caused her to bite back a grin and shake her head. She knew they wanted her to do something with her evening, maybe even _someone_ , but that isn’t what she had come out for. Y/N had joined Donna and Jody to spend time with her friends, to let go of her everyday troubles. Not to end up in bed with a stranger.

In the time that was spent silently communicating with her girls, she hadn’t noticed that Dean had also spun his stool around, leaning casually back against the bar as he sipped on his whiskey.

"If you don't mind me askin', ma'am, why are you sitting here on your own and not down there dancin' with your friends?" He wondered, causing her to glance over at him, the silence between them broken.

She hesitated for a second, allowing her mind to process that he was indeed talking to her, his piercing stare giving it away.

"I don't dance," she replied simply, shaking her head.

Dean let out a soft chuckle, peeking his pink tongue out over his lips. "I find that hard to believe."

She frowned, her brows connecting in the middle at his disagreement. "Well, it's true."

The man next to her pushed himself off of the bar, resting his drink hand against his trouser clad thigh as he allowed his smile to broaden, little crinkles appearing at the corner of his eyes. Y/N felt an odd feeling roll within her when she caught his gaze. She couldn’t deny that the man next to her was handsome; chiselled jawline, plump pink lips, eyes that could outshine emeralds. His physique was slightly hidden beneath his uniform, yet she could still make out his broad shoulders and strong legs.

"So, you're telling me that you don't dance around your kitchen at home with the radio on? That the man in your life doesn’t grab you by the hand spontaneously to sway you gently against him, any opportunity he has?" Dean coaxed, bringing his drink to his mouth for another sip.

"That's completely different," Y/N argued, her cheeks flushing partially as she heard him chuckle next to her, "and no, there is no _man_."

She rolled her eyes as his laugh reverberated between them, her fingers clutching tighter to the glass in her hand. In her peripheral vision, she watched as he turned to place his now empty tumbler on the bar, signalling the barman for a refill.

"So you do dance," he started, his words carrying on a chuckle, "just not in public."   
  
Y/N did not have a witty comeback, her mouth opening and closing without words passing her lips. Instead she gestured towards the rest of the room, her sights now on the groups of sailors that were taking over The Cove.

"Well, it looks like your brothers in arms are having fun. Do you not want to go back over there and join in on it?" she fired back, but Dean just shook his head, leaning back to grab the newly refilled glass of whiskey.

"I spend months on board a ship with them, so when I come ashore, I like to give myself some space from it all," he explained, bringing the amber liquid to his lips and appreciating its taste.

Y/N could respect the need to be solitary, with her enjoying her own company and the peace it brings more often than not. She found the man next to her intriguing. His words seemed honest and his smile genuine but she had fallen for that ruse before. As her gaze went back to the sea of people in front of her, she wondered how long the sailors were going to be around. Usually, it could be anything from a night to two weeks. 

"How long are you here for?" she asked Dean inquisitively, her curiosity itching away at her.

“Including today, eight days and we leave on the ninth,” he replied, his voice as smooth as honey as he smiled at her warmly. 

Y/N nodded, her lips pursing in thought. “A good week of time off then.”

“Maybe.” Dean shrugged, looking back down at his drink as he swilled it around the glass.

The conversation reached a natural end, Y/N not knowing how to continue or if she wanted to; it seemed right to leave the man to his own company. As she continued to watch the crowd, she noticed her friends weaving through the bustling groups of patrons. Their arms linked so they wouldn’t lose each other as they locked eyes with Y/N, eager to be by her side again.

“Enjoying your evening, ladies?” Y/N asked them once they got closer, a small giggle leaving her lips when she noticed the tipsy state they were already in.

“Oh you have _no_ idea,” Jody replied, her eyebrows wiggling causing Y/N to laugh louder.

“He’s a cutie, huh?” The blonde next to her suddenly announced, shoulder bumping Y/N with a force that made her hold onto her stool.

“Donna!” she exclaimed, hoping to God that the Lieutenant Commander had not heard the words that had left her mouth.

“She’s not wrong,” her other friend commented, a little snort sounding from her as she took a note of Y/N’s shocked face.

“Jody!”

“Sweetie, you’ve been here for a little under an hour and you have not moved from this spot,” Jody said, a knowing look on her face as she stared down at her. 

“Because I’m comfy,” Y/N retorted, a frown appearing along her brow, “and because an asshole sailor decided to share his _delightful_ charm with me.”

“Y/N…” Donna sighed, both of her friends immediately becoming concerned, their faces dropping after hearing what had happened.

“You know, I’m just going to head home,” Y/N announced, downing the rest of her martini in one gulp. She turned in her seat, sliding the empty glass along the bar before she picked up her purse. “You girls stay, have fun. This scene isn’t for me.”

Donna and Jody exchanged worrisome looks, the blonde taking the lead. “We’ll grab our bags, give us two seconds to say good--”

“No, seriously, you guys stay. Don’t let me ruin your night,” she cut in as she slid off her stool, turning to fix her dress and to smile at her friends. “It’s fine, honestly.”

Y/N was telling the truth, the look in her eyes told them that. She just didn’t want to be surrounded by drunk shipmates, nor did she want to drink at the bar alone when she could grab a bottle of wine at home. Also not wanting to be a downer for her friends, she was absolutely insistent that they stayed, especially since she loved them for trying to get her out.

“We love you,” Jody announced, both of the girls bringing Y/N in for a tight hug.

“I know,” she smiled, kissing both of their cheeks in turn. “I love you both too.”

Y/N turned on her heel and headed towards the exit of The Cove, weaving her way through sailors and their many admirers. Her eyes glanced over the couples that were dancing, how intimate and close they looked, how _in love_ they looked. She couldn’t help the scoff that passed her lips. It was all a lie.

She’d been that girl once, the one that was hopelessly smitten with a sailor that had been passing through. He had promised her the world and more, his words like a smooth liquor. She lapped them up, hung off of everything he had to say. Y/N thought they were the real deal, that she had found her soulmate and she was to live happily ever after. Yet, her heart got broken. He left on his vessel, with a promise to call and write, only to hear nothing for months. The next time his ship docked, she was unaware and caught him down an alley tongue deep in another woman. Thus solidifying her views on men that surrounded her.

Y/N still felt the burn of her tears when she thought about that memory and suddenly she became desperate for fresh air. She fought her way through the crowds to get to the exit, stumbling past the bouncer before the palm of her hand found the cool stone of the building's wall, helping to steady her. Chest heaving, she quelled the sobs that wanted to leave her and with a shaky hand, she composed herself and straightened her outfit once more.   
  
“Ma’am?” That familiar deep voice carried softly to her ears, causing her to turn around and be greeted with the concerned gaze of the man who stood up for her.

“Please leave me alone,” Y/N breathed, padding her cheeks with her fingers to ensure no tears had fallen as she turned away from him.

“Let me walk you home," he offered, his hand wrapping around her wrist gently to gain her attention.

It was a move she snapped herself away from, her palm close to her chest as she faced him. She could tell by the look on his face that he knew he had made a mistake, yet fueled with hurt and anger from her memories, she didn’t care.

"That's cute, Mr. Winchester, but it's not on my agenda to end up in bed with a sailor this evening, thank you," she spat, watching as Dean’s eyebrows reached his hairline, his hands up in surrender. 

"Woah, hang on a minute, I just wanted to make sure you got home okay," he admitted, his eyes searching hers as she studied him.

"I don't _need_ to be walked home," Y/N protested, flinching when a group of inebriated sailors stumbled past her, most of them giving her an eye.

"Well, with all these drunks around--” he started, gesturing at the men that had just walked past, “- and with what happened with Trenton in there, I would feel much better knowing you got home safe."

"Why?” she immediately snapped, shrugging her shoulders, “If not to get into my bed then why would you possibly want to do such a thing?"

She saw Dean take a deep breath, sliding his hands in his pockets. "Because believe it or not, not all of us sailors are assholes."

His words had her wince slightly, but Y/N managed to keep her expression internal. It was now obvious that he had definitely overheard her conversation with Donna and Jody moments earlier. However, she didn’t feel bad for what she had said. In her experience and to be proved by her encounter with Cole, sailors _were_ assholes.

"Seeing is believing, Mr. Winchester," she countered, turning around to start the fifteen minute walk back to her house.

"Then let me prove it to you," he shouted after her. His voice was followed by his footsteps, eager to catch up with her strides.

"You think me letting you walk me home will be enough proof?" she asked, exasperated and slightly annoyed by his persistence.

"No," he told her honestly, stepping out in front of Y/N to stop her in her tracks, "but it would be a good place to start."

She took a chance and looked up into his eyes, the sea of green calling to her like a lighthouse shone in the night. There was something about Dean Winchester that spoke to her and it was something she couldn’t put her finger on. He was intriguing, he was insanely handsome and he was acting like the perfect gentlemen; so what was the catch?

Y/N didn’t feel uncomfortable in his presence, quite the opposite, really. She could be smart about this, take the most well lit route home and keep a hold of the keys in her hand, in case she needed to jab the Lieutenant Commander and make a run for it, if he were to make a wrong move. But after Cole Trenton had made her feel so uneasy with his confident advances earlier, she had to consider the point that the green eyes man just made; it was not safe for a woman to be alone in these parts of town, with all his drunken subordinates roaming around.

"You can walk me to the end of my street," she instructed, a huff following her words.

"Good enough for me," Dean concluded, offering her a calm smile as he gestured for her to lead the way.

With a nod, Y/N started the journey home with her new sailor friend at her side. He didn’t pressure her into talking, neither did he start a conversation, he just walked by her side with his hands in his pockets. She was thankful for the silence, and in a way she was glad that Dean wasn’t trying to force small talk. Instead, she just admired the views as she put one foot in front of the other. The docks were first, her ears filling with only the sound of the gentle waves crashing against the wooden beams. She felt grateful for the cooling night breeze, moving stray hairs from her face. The wind also carried the smell of Dean’s cologne, and she couldn’t help but appreciate the scent.

After the docks came the small strip of beach, the street lights basking the sand in a golden glow, making it look enticing for late night strolls. Y/N would love to be walking barefoot down the shoreline, but considering current company, she continued her way to her home. She didn’t realise how fondly she was beholding the seafront as she passed, missing the way Dean looked at her as he kept close to her side, his mouth twitching slightly in smile. The serenity between the pair was anything but uncomfortable, which surprised them both.

Finally, after crossing the quiet road, Y/N saw her house in the distance. She breathed a small sigh of relief, knowing that she was soon to be home, curled up in her comfy clothes. She would light a few candles, pour herself a glass of wine and grab her favorite chocolate from the fridge before snuggling down in her bay window that overlooked the sea, current book in hand.

"This is me," she announced as she came to a stop, nodding her head in a gesture to the street. 

Dean stopped next to her, his hands still in his pockets as he rocked on his heels. "If you don't mind, I'll wait right here until I see you go in through your front door."

"There's no one around, I'll be fine," Y/N insisted, holding her arms out wide as she looked around, clutching her purse and keys tightly. 

"Then you won't mind me waiting, just in case," Dean countered, the knowing look on his face causing her patience to wear thin.

"Okay, enough with the gentlemanly act. I get it," she huffed, rubbing at her forehead.

"I don't think you do," Dean started, "because you _still_ think I'm an asshole," he continued, taking his hand out of his pocket to rub at his chin. "Lucky for me, I've got seven more days to convince you otherwise."

Y/N shot him a wide eyed, incredulous look. "And what makes you think I'm going to even _let you_ have a chance to convince me?"

She was in utter disbelief, her mouth parted slightly as her brow stayed furrowed while awaiting his answer. _This cocky, full of himself, son of a--_

"That inquisitive look you got twinkling in your eye," the sailor spoke softly, allowing his one hand to now drop by his side.

Y/N hadn’t known this man for more than a couple of hours and yet here he was, calling her out like he had known her for years. She had to admit to herself, though, she was curious about this guy, attracted even. Yet, that niggling doubt in the back of her mind was rattling its cage louder than ever. What if he is exactly the same as the others? What if he breaks her heart just as bad as before? What if...

What if he was the one to put her back together again, to make her believe in love once more?

"I'm working most of this week," she muttered, her arms crossing over her chest in a stubborn manner. If he truly wanted this, truly wanted _her_ , she wasn’t going to make it easy.

Dean’s lips started to tug upward. "Luckily, I’m free. I'll work around your schedule."

"You don't even know my name," she countered, scanning each of his eyes for any signs of trepidation.

"You'll tell me when you're ready," he responded cooley, tilting his head to the side ever so slightly. He was infuriating her.

"Do you ever give up?" Y/N wondered, her foot tapping against the stone sidewalk.

Dean chuckled softly at that, his tongue peeking out to pull in his bottom lip. "Not really, no."

Y/N huffed loudly, looking over her shoulder at her home before turning back to the sailor in front of her. It was just one date. A couple of hours at most, that she would have to spend with him and this time, she would go in guarded. She wasn’t about to get burned twice.

"I finish work at 2 pm tomorrow," she announced, a softer tone to her words.

"Then I'll see you at 2 pm," Dean agreed. "You work around the docks, right?"

To that she smiled, taking a moment to truly appreciate the man in front of her as she thought about her answer. She could tell him where she was employed, but where would be the fun in that?

"Goodnight, Mr. Winchester," she announced, turning in her spot before she began to stroll down the street, the corners of her mouth pulling slowly upward as she played with the keys in her hand.

With a grin, he could only call after her. "Call me Dean."


	3. Chapter Three

**Notes for the Chapter:**

> Hey Guys, hope you enjoy chapter 3! <3
> 
> Hope you're all keeping well and safe. Much love to you all.

The afternoon sun provided rays of warmth through The Daisy Chain’s windows, the small chatter of patrons providing a low hum across the space. One by one, the booths and tables were vacated as the rush of lunchtime had just finished, the diner becoming quieter once more, giving the staff the chance to catch up before customers arrived for dinner. 

In the far corner and while wearing a soft smile, Y/N assisted an elderly couple who were just about to leave. She stood back as the husband assisted his wife out of her seat, his aged hand sliding into her palm before he continued to hold on tightly, escorting her out of the establishment. That was not before he slipped the waitress a ten dollar bill as a tip, the kind gesture warming her heart. She watched on as the pair left, waiting until they were walking away down the harbor before she began to clean their table. Her gaze was still locked on to the way they were with each other, the looks they shared were ones that proved that love can still exist, even after being with each other for so long. It was a love that she had often dreamed of, acts like the one she had just seen igniting her hope that maybe, someday, she could experience an ounce of that happiness.

Y/N slid the money she had been gifted into the front pouch of the apron that was tied neatly around her waist, protecting the bottom half of the yellow cotton midi dress that she was wearing. Bending forward, she blew away a piece of hair that had fallen from her french braid from her face, as she continued to place all used dinnerware onto the wooden tray she had brought from the kitchen. She then reached behind her to collect her wash bowl, reaching in for the wet dish cloth before sliding the material over the station, working on cleaning the tiny little brown ring stains that had been left by the fresh cups of coffee that had been consumed.

Satisfied with her work, the waitress turned in her place. With the tray resting on one hand and her bowl placed on her other hip, Y/N made her way back towards the kitchen, giving Rufus a warm smile as he cooked a fresh burger, a towel slung over his shoulder. On the other end of the counter, the diner’s phone began to ring, her attention now focused on the chime as she moved to swiftly answer it, only to be beaten by Jody who gave her an appreciative wink.

She headed to the storage closet, intent on taking out the mop and bucket to clean the floors of the back section of the diner. Stepping into the darkened space, her hand automatically reached up for the long beaded chord that dangled from the ceiling, pulling down sharply, she placed her hands on her hips as the room illuminated with light.

“What do you think you’re doin’?”

The southern tone made Y/N jump, her hand flying to her chest as she turned around, wide eyed. She was met with the curious arched eyebrow of Donna, leaning against the wooden frame of the door.

“Working,” she replied, her tone higher than normal, thanks to the shock she had just received.

“Oh no, you’ve got a certain sailor to get ready for!” the blonde declared, waving her hands in front of her as she pushed off of the woodwork, her hands wrapping around the bicep of Y/N as she began to march her to the staff room, the storage closet long forgotten.

“How on earth do you know that?” Y/N questioned, her face holding a quizzical look as Donna just grinned. It was then that it clicked; the earlier diner phone call which Jody answered. “Nanna.”

“I’m under strict instructions by Flo to ensure her granddaughter is ready for her date,” the midwestern woman informed her, her smile wide and her voice giddy as she continued on her path.

“Which you didn’t tell us about,” Jody piped up as they passed her office, offering Y/N a knowing look.

“There’s nothing to tell,” Y/N squeaked, shaking her head. Yet, the boss who was currently marching her to the back room deadpanned her a look, not believing a word that had left the waitress’ lips. “There isn’t!”

“Sure, and I’m the First Lady,” came the sarcastic remark from beside her. She couldn’t help but smile at her friend's comment.

“I don’t even know when he is going to stop by,” Y/N lied. Well, it was sort of a lie. She had told the green eyed sailor to stop by at two, but considering he had no idea where she worked, she didn’t know if he would show or not.

“All the more reason to let me help you get ready,” Donna responded, turning Y/N around in her hold before pushing the waitress gently down in the chair behind her.

Opening her mouth to argue, she promptly held onto her words, knowing that it would be wasted on the woman who was currently bustling around her. Donna had pulled out her selection of make up, a hair brush and wipes to help to freshen her face. She sat and stared at her hands as she felt the blonde pull on the tie that was holding her braid together. Her locks became loose around her face, deep waves framing her features as she felt Donna begin to work on it at the back.

“I can’t believe my Nanna called here,” Y/N spoke softly in disbelief, her words carrying over the quiet. Crossing her arms across her chest, she closed her eyes, trying to enjoy the feeling of her friend combing through her hair.

“She wants to see you happy, sugar. What’s wrong with that?” Donna queried, slowing her brushing as she looked over the features of her pamper subject.

“Nothing,” the waitress sighed, beginning to pick at her fingers. “But she knows my views on sailors, so I don’t get why she’s pushing me.”

Releasing a deep breath, Donna placed down the hairbrush on the table in front of them before promptly pulling out some blusher. “Y/N, it’s been over a year since you have done anything that is just for you. You never put yourself first and you condemn any man that even remotely gives you the eye.”

“I do no--” Y/N began, but a prompt look from the Minnesotan beauty caused her to bite her tongue, knowing that she was _actually_ right. Choosing her next words carefully, she pulled her bottom lip between her teeth in thought. “He’s only going to be in my life for five minutes, so what’s the point?”

Donna returned a knowing gaze as she sat in front of her, a blusher brush in hand. “The _point_ is that if you let him, he may be in your life longer than that.” 

“He’s a _sailor_ ,” Y/N recounted, a small scoff leaving her lips. “Well, a Lieutenant Commander, but the rule still applies.”

“Give him a chance, honey,” her friend tried to reason, swiping the pinky hue across her friends cheeks, “and if he breaks your heart, then you’ll be damn sure he won’t be tootin’ his own horn by the time I’m done with him.”

The wink that was sent her way, caused Y/N to chuckle. She knew Donna had good intentions at heart, but she still couldn’t help but to feel apprehension when it came to this date. She tried her hardest to keep those thoughts at bay as she closed her eyes, trying instead to focus on the sensation of her personal makeup artist sweeping eyeshadow across her lids. This time was going to be different, as she wouldn’t allow the man into her heart like she did the other. She would go in guarded, her walls high and impenetrable.

“Just beautiful,” Donna uttered, after she finished the final touches of Y/N’s lipstick, leaning back to admire her work before passing the waitress a mirror for her to examine the look herself. She smiled when she saw her reflection, appreciating the effort that her boss had made, her look natural with only a slight smokey eye. It perfectly complemented the yellow dress that she was wearing. 

It was then that the bell above the diners entrance signalled, causing both women to look at the clock that was hanging on the wall, the hands showing 2pm. Donna rushed from her seat, taking a peak from the staff entrance to the front of the diner.

“He’s right on time,” she announced, turning back around to usher her friend from her chair. “This is your moment to shine, sweetcheeks.”

Y/N hung her purse on her shoulder by its strap, before she staggered down the narrow hallway, her heels slightly digging into the floor as she was pushed further towards the entrance. It was only when she got to the edge of the kitchen that she stopped, her eyes falling onto the man that was standing in the diner’s doorway, one hand in his pocket, the other by his side as he looked around the room. The sailor looked a lot more casual today than he did last night. His dress whites had been exchanged for an untucked, light blue button down shirt, the sleeves rolled up to his elbows. His legs were now wrapped in blue denim, paired with grey canvas Rockport slip ons. She would be lying if she said that she wasn’t the tiniest bit attracted to him, even more so after seeing him in clothes that brought out his physique.

She noticed how he caught the attention of Alex, another one of the waitresses and Jody’s adopted daughter, and she watched as he smiled softly as the young girl approached him.

“I hope you don’t mind me asking, ma’am, but does a lady with Y/H/C hair work here? Yesterday, she wore a white blouse and a polka dot skirt, she went out to The Cove last night.”

His gruff voice carried through the diner and it caught her by surprise that he remembered the details of her clothes. He paid attention, she would give him that.

“Oh, I think you mean Y/N,” Alex quipped. “She’s in the back. I’ll go get her.”

Dean gave a grateful nod to the young waitress before he began to look around the room as he waited. Y/N tried to shrink out of sight, hoping not to be spotted just yet as she wasn’t ready to step into his spotlight. She just wanted to sneak back into the kitchen and hide herself away, not ready to face the reality of the situation. Yes, her friends had a point, maybe she should make her return to the dating scene, but why did it have to be with a sailor? It ended in tears the first time, so what would make this time any different?

“I didn’t want him to know my name yet,” Y/N uttered under her breath, unaware that Donna was standing right behind her, tugging at the string of her apron to unwrap it. 

“Girl, you’re going on a first date, he _needs_ to know your name,” the Minnesotan boss chuckled, balling the apron in her hand before she started to usher her friend to walk. “Now, come on. Move.”

Shooting her friend a quick look, Y/N took a deep breath and placed one foot in front of the other. She focussed on her hands unhooking the counter top to step through, and not on the man who was beginning to beam at the sight of her. As she turned around to close the hatch behind her, she noticed Donna beginning to lean on one hand, a dreamy look on her face as waited for the event of the day to unfold. With a smirk, Y/N reached for a napkin and slid it in front of her friend as she walked past.

“You’ve got a bit of drool just--” she started, signalling to the corner of her lip before she turned away.

As her gaze caught the green irises of her date, she watched how his small smile evolved into a broadened grin, his head slightly towards her in greeting.

“Afternoon ma’am,” he spoke softly, his eyes never wandering from hers. She was somewhat perplexed that he chose such a formal acknowledgement, especially considering he just found out her name, yet his gentlemanly gesture didn’t go amiss.

“Mr. Winchester,” she returned, holding his stare as she crossed her hands low in front of her.

“Are you ready?” His question was followed by him opening the diner door for her, his arm outstretched before he signalled for her to lead the way.

Y/N moved forward. “Let’s see what wild adventure you have planned.”

She took a confident step through the door and onto the docks, her beige, slingback ballet flats providing a light tapping sound against the wood as she walked. Biting her lip slightly, she tried to stop her giddiness at the situation from seeping out. It didn’t help that when she turned around, she saw her Daisy Chain family all staring at her with beaming faces. She couldn’t help but roll her eyes at her friends’ antics as she waited for her date to close the door behind him.

A gentle breeze blew over the couple as they began a slow stroll down the harbor, the sound of gulls carrying on wind. A moment of silence had washed over them, both admiring the views they were walking towards. Y/N was following the Lt. Commander’s lead, allowing him to steer their direction as she crossed her arms across her chest, her fingers wrapping around her biceps.

“I’m surprised you found where I work, and at the time you said too.” She couldn’t help the teasing tone in her voice, honestly surprised he had made it at all, considering she hadn’t made it that easy. Moving some stray hair from her face, she looked at the man to her side, her palms that were laced with nerves began rubbing at the tops of her bare arms as she matched his slow pace.

“I like to be punctual for a date,” Dean replied, a casual shrug of his shoulders as he slid his hands back into his pockets. Y/N wondered whether it was from being nervous, but surely a man this good looking wouldn't be anxious about his company.

“So how _did_ you find me?” she wondered curiously, her mind reeling with the possibility that maybe he had gone back to The Cove to do some digging.

The sailor let out a single shy laugh, his white teeth peeking through pink lips. “Well, I started at the end of the docks and went into every shop until I found you.”

Almost immediately, Y/N let out a chuckle at the prospect. The harbor was home to twenty plus businesses, the idea of this man searching each one just for her was too much. It was only when she noticed how he wasn’t joining in with her laughter while one hand was now rubbing at the back of his neck, she realised that maybe he was telling the truth.

“Wait, you’re serious?” Her amusement faded somewhat when she saw him slowly beginning to nod, and she wanted the ground to swallow her whole.

“Asked every person in the harbor, every shopkeeper, even an overly friendly fisherman’s wife.” He licked his lips, a hand coming to rub at his chin. With a quick glance over her shoulder, she suppressed her amused look, knowing exactly who he was talking about. 

“Ah, Mrs. Fawcett,” she remarked, swallowing down a chuckle. She was indeed a fisherman’s wife, one that was rotund, short and renowned for her womanly ways. “She’s well known for her enthusiasm when it comes to helping men.”

“R - really?” Dean stammered, his eyebrows hitting his hairline at the realisation, his face paling at the thought of the amorous lady from the docks. “Then I guess I had a lucky escape.”

“Maybe,” Y/N sniggered. “Although I will tell you, she doesn’t give up easily.”

The look that the Lieutenant Commander wore, was a look that she would never get tired of. Never in her life had she seen a man look as mortified as Dean Winchester did in this moment. She had seen the effects Mrs. Fawcett had on people. She was like an overbearing mother who had nothing but kindness in her heart, yet when it came to men, she would eat them alive. A lot of passersby come to the conclusion that her husband must be none the wiser, long days at the sea can cause a woman to be lonely. Yet, Y/N was convinced that the man who married the woman in question knew every detail, he just turned a blind eye to her hungry libido to give himself a rest.

Turning the final corner of the harbor, a smile adorned the woman’s lips, one that got wider as they seemed to be approaching the familiar ground. Was this really where he was taking her for their first date? Her mind cast behind to the previous night, when he had walked her home past this very beach. Surely he hadn’t remembered this detail, as well as what she was wearing.

“The beach?” she questioned, her gaze falling onto the calming sight in front of her.

“I saw the way you looked over at this shore yesterday. I thought this would be a good place to start,” Dean told her, his voice soft and gentle as he led her off the docks and onto the sand.

She watched, perplexed as she tried to wrap her head around this situation, her defenses around her heart on alert. The sailor hadn’t even been in her life for twenty-four hours and yet here he was, already beginning to bang on the walls she thought were unbreachable. Yet, she refuses to let him in. A few nice gestures meant nothing to her. Anyone can act for a day.

“I have missed this feeling.” His sigh broke through her thoughts as she noticed how he had taken off his shoes, his feet already bare on the golden grains.

“Has it been a while?” she questioned, balancing on one leg as she proceeded to follow suit, pulling the flats from her soles and burying her manicured toes into the warmth beneath her.

“Three months.”

His response didn’t shock her, she knew that sailors could be at sea anywhere between three to nine months at a time. Still, not walking on land for that long, is not something she could picture. She would miss the different sights and sounds, the array of people, the places offering an escape when things got too much. Being trapped on a metal cruiser didn’t seem all that appealing.

“I couldn’t imagine three months without tucking my toes in the sand,” she spoke honestly, holding her shoes in one hand by the backs as she slowly began to walk towards the ocean.

“I get by. Makes me appreciate these moments a lot more,” he replied, nonchalantly. “Would you like some water?” he asked her, pointing to the little beachfront shop they were passing.

Y/N nodded, grateful that he would think ahead to get them a beverage, especially on this warm day. All she could do was offer him a smile as she watched him interact with the staff member. Her words were lost when she thought about not being able to have this on her doorstep every day and it filled her with sadness. In all of her anger that she held towards sailors, she had forgotten about what they sacrifice. Their family, their lives, their ability to dip their feet into the sand whenever they felt like it.

“Thank you,” she gratefully told him when she accepted the bottle he had outstretched to her. The look he gave her was one that told her ‘no problem’ without him having to mutter the words.

“So, I take it you come here often?” his question broke the momentary silence that had fallen over them and she couldn’t help the affectionate expression that broke out on her features.

“I do. It’s one of my favourite places to be,” she admitted, her voice full of admiration for the seaside that held many of her memories.

“I can see why,” Dean agreed, his green irises taking in the warm scene in front of him.

She followed his line of sight, her own gaze focusing on the soft waves that were rolling into shore, the few gulls that were bobbing along the surface of the water, their feathers ruffled by the slight breeze that kissed the surface of the sea. The summers sun basked down on them, creating a warm haze that decorated everything with a tinge of gold. It was a small slice of heaven, that Y/N was sure of, but this was nothing compared to favorite spot at the coast, the one where she spent most of her time.

“You’ve not seen the best of it yet,” she informed him, adding a little side glance his way.

“Then by all means, ma’am, show the way.” He gestured for her to take the lead and that she did, her heart doing a slight jump in her chest as she took in the way the summer hue had hit him just right.

Swallowing down the sudden rise in feelings, she took charge and steered Dean towards the edge of the water, warm waves lapping at their feet as they followed the shore line. Y/N had a place in mind to take the Lieutenant Commander, a place that she always escaped too to lose herself in her own thoughts and ideas. Normally, she wouldn’t share such a place with a stranger, but there was something about the man who was padding in the ocean next to her, that told her she was safe.

Over the next fifteen minutes, Dean proceeded to ask her about her day, how work had gone and how she had gotten to know the owners of The Daisy Chain. At first she was thrown by the interest he was showing, but when she turned to see the amber flecks that glistened in his eyes, his intrigue reflecting back like a mirror, she realised he was being genuine. Not once did he expect her to return a question. He was more than happy to find out all there was to know about the girl with the flyaway skirt.

“Oh, stop, don’t move!” Y/N suddenly announced, her arm flying out to the side of her, water bottle nearly hitting Dean square in the chest. The abrupt movement caused the sailor to panic slightly, one bare foot hovering over the shallow depths of water beneath it.

“Sea Nettles?” he asked, cringing slightly at the thought of their sting, a little worried that one may be closing in on him.

Y/N looked up at the man who looked more like an injured flamingo than a brave Lt. Commander. “No,” she laughed, wholeheartedly.

Placing her shoes and water bottle next to her on the beach, she hiked her dress up slightly to prevent the edges from getting wet. She stooped where she stood, submerging her delicate hands into the water to pull on the item that she had spotted buried in the sand. Her eyes lit up when she noticed what it was, the corners of her mouth pulling up in wonder as she slowly began to stand.

“What have you got there?” Dean asked her, curiously as he slowly lowered his elevated foot, providing himself with equal balance once more.

“From the looks of it -” Y/N started, brushing away some left over dirt with her thumb, “- a channelled whelk.”

“A what now?” The perplexed look from the green eyed man next to her didn’t go amiss and she couldn’t help but find it adorable. She continued to look at the find in her hands.

“It’s the shell of a large predatory sea snail,” she informed him, the information easily flowing from her as she examined the exoskeleton she was holding. She felt the warmth of his body radiate next to her as he stepped closer to look at the soft blue and white pattern of the object she was holding.

“Do you collect them? Seashells?”

“Only if they catch my eye,” she replied, a small sigh passing her lips. “They’ve all got a story to tell, you know?”

“So what does this one tell you?” he asked her softly, his eyes glancing up to catch her gaze. She was unaware at how close they were, their noses just a few inches apart before she cleared her throat and looked back to her hands.

“That he lived a good life, a happy one. He must have been a good age due to the size, not many defects so not many injuries. Probably died of natural causes.”

It took a moment for Dean to register what she had said, his brows knitting together slightly as he leaned back to look at her.

“You got all of that from a shell?” he questioned, equally stunned and impressed by her explanation. Y/N let out a chuckle as she started to unhook the clasp of her purse, aiming to shelter her trophy inside.

“And my imagination.” Y/N winked before bending down to pick up her water and shoes to continue on the walk.

A low yet warm laugh left his lips. “So apart from beach walking and collecting the houses of snails, what else do you do in your spare time?”

Taking a quick glance to her right to find the sailor was still looking down at her intently, the genuine interest flickering in his features, she allowed her walls to crumble just the tiniest bit.

“I write.” Her admission was short but it was something she held dear. If she wasn’t reading a book, she was writing her own. Y/N constantly carried a notepad and pen in her purse, never knowing when inspiration would strike and when she would need to write down an idea. 

“You’re an author?” Dean’s question and the tone of his voice, gave away that he was truly fascinated by her hobby. She was touched, as well as a little confused, her head and her heart in a war over how she should feel.

“Not published or anything,” she explained, swinging her shoes in her hand by her side. “I just enjoy escaping to another little world for a little while.”   
  
“Will I see anything from you soon?”

“Not a chance,” she chortled, shaking her head as she turned to face him. “I don’t write the kind of stuff sailors would read.”

“Now my curiosity is peaked,” he grinned, an eyebrow raised as she laughed.

She was quick with her counter. “And it can stay that way.”

With smiles resting on both of their faces, Y/N quickened her step as they got closer to the clearing she wanted to show the man who accompanied her, her feet splashing in the water beneath her. Through some trees that were close to the sea edge, there was a small opening. Moving the branches to the side, placing her bare feet carefully in between the shrubbery that covered the sand, she revealed an intimate part of the beach. Rockpools were scattered over the land, piles of driftwood rested on the golden grains and it was secluded, it was quiet.

As she held the branch aside, Y/N turned and nodded her head in gesture for Dean to follow her, his eyes widening as he took in the view around him. Watching him take a tentative step forward, his large hand coming to take a hold of the branch from her, she stepped back before moving to find her usual spot to sit in. She unhooked her purse from her shoulder, placed her water bottle and shoes in the sand next to her before tucking her dress under her legs as she sat in the sand.

“This is beautiful,” the sailor admitted after which he blew out a breath, taking in every detail that he could. He then turned to face her, his palm outstretched as he gestured to the space next to her. “May I?”

Y/N nodded and watched as he settled down beside her, his back resting against the wood as he buried his feet into the sand, his wrists resting on his knees. A calm silence fell over them, the only sounds to be heard were those of the waves and the trees as they blew in the gentle breeze. Out of her peripheral vision, she took note of how Dean was taking a moment to truly appreciate his surroundings as he unscrewed his water bottle to take a generous sip, something that she copied as she continued to cast a glance at the man close to her.

There was something about the Lieutenant Commander that pulled her in, the inquisitive side of her itching to learn more about the man who had decided to take an interest in her. She still hadn’t gotten her head around the fact that he wanted her, that he chose the closed off waitress instead of a much easier option at The Cove. Out of all the girls who were so willing to throw themselves at any sailor, here he was, sitting in silence next to _her._

Y/N tried to quell the sabotaging thoughts in her head, that maybe he enjoyed a challenge, that maybe this would be all the more satisfying for him when he got her into bed. Yet, his actions called out to her. The way he walked her home without expecting anything in return, the way he had searched the docks and escaped Mrs. Fawcett’s clutches just to find her. The way he showed an interest in _her_. He even knew her name, something she hadn’t been ready to tell him, yet out of respect for her decision the previous night, he had chosen not to use it.

As the afternoon sun bounced off the lapping waves of the shore, it was then she decided to find out more about the mysterious sailor next to her. Asking him questions about his day to start with, wanting to return the kindness he had shown her so far. He answered them, a soft and warm rested expression appearing on his face as she listened to his tales. He told her about his morning, finding what to wear for his first full day of his leave, how he wanted to start his search early in case he had to resort in sending out some of his friends to help locate the woman who he was supposed to go on a date with. It was a moment that was broken by the sound of her ringtone, resonating from deep within her purse, causing her to startle.

“Do you need to get that?” he asked her gently, not phased at all by the call she was receiving. Pulling out her phone, she playfully rolled her eyes when she saw who was trying to contact her.

“No, it’s just my Nanna. She probably wants to check in and see how it’s going.” She let out a small laugh, shaking her head as she quickly fired her a text. “I love her but she doesn’t have the greatest timing.”

Y/N knew it wasn’t an emergency as her phone wasn’t lighting up like it was the center of a stage show. Nanna Flo was just being nosey and wanted to know every tiny, intricate detail about this date.

“She’s really special to you, huh?” Dean asked her, the question making her smile warmly. The look on her face must have given her feelings away.

“She is,” Y/N confirmed, placing her phone deep back within her purse. “Her name is Florence and she has been through some amazing adventures in her time. She’s all I have left now.” She quickly swallowed the lump that had formed in her throat, clearing her throat promptly before turning her head to look at the man next to her. Not wanting to go down that road to her past. “What about you? Anyone important in your life?”

Dean gave her a look of endearment, one that told her she understood and that he wouldn’t push, before he leaned forward off the driftwood, his hands still rested in his knees. “I have my mother and a younger brother. They’re back home, not too far from here actually. My father...” he started, before taking a deep breath. “Well, he died before he had the chance to retire.”

“I’m sorry,” Y/N consoled, her words soft as the gentle wind that blew around them. She had felt that pain, more than once.

“It was a few years ago when we lost him. I always wanted to follow in his footsteps, so here I am,” the sailor told her truthfully, the corner of his eyes crinkling slightly as the words left his lips. 

“He served too?” she asked him, genuinely intrigued; this was the backstory of what made him who he was today.

“Most of his life.” Dean told her, nodding his head slightly as he gazed over the deep blue. The moment had become sombre, only slightly, both of them feeling the pain of loss they had experienced, yet neither of them knew the depths of the scars that had been created.

“Okay, Y/N, tell me something else,” he announced suddenly, collecting himself as he moved to face her, his eyes glancing over her features as she turned to him.

“Like what?” she smiled, grateful for the upbeat change.

Dean blew a breath, his lips vibrating together as he thought, his hands swinging around as he tried to think of a question. “Biggest pet peeve?”

It was random but it was one that made her chuckle, feeling the ice between them well and truly break at this moment.

“Ah, well. It’s these men that come in on boats, ‘sailors’ I believe you call them,” she teased, chewing at the inside of her mouth as she held in a chuckle.

Dean shot her a look before he threw his head back at her joke, sounds of joy leaving him as his shoulders shook. She couldn’t help but join him, the sound of his laughter infectious, warming her soul. 

“Ah!” The sailor suddenly yelped, shooting to stand up almost immediately and Y/N held her breath for just a moment, wondering what had just happened as the man beside her tried desperately to look over his shoulder.

It was then that she saw it, a small crab hanging off the backside of his jeans and her amusement bellowed from within her once again. Her arm held onto her stomach as she tried so hard to breathe, while the sailor looked down at her with a pained and bewildered expression as he winced. 

“Calm down,” she managed, trying to dim her laughter. “It’s just a Fiddler crab.”

“Well I would appreciate it if he would fiddle with something else,” Dean shot back immediately, his tone light and cheerful, despite his teeth being gritted as he tried to reach around for the small marine animal, clearly finding this situation entertaining too.

She watched on as he detached it’s pincer from his clothes, her eyes roaming over his bottom half. She couldn’t help the flush that blessed her cheeks, knowing that she was practically staring at his behind but she had to admit, it wasn’t a _bad_ thing to look at. Rolling her tongue over her lower lip, she pulled the flesh between her teeth to try and stop an amused sound from leaving her.

“He took a liking to you, obviously,” she stated, observing as Dean placed the crustacean back into the sand, the little creature scurrying off in another direction. It was then he looked down at her, his green eyes twinkling when she couldn’t help the next comment that passed her lips. “It’s not unusual for sailors to get crabs on their first date though, is it?”

The smile she was wearing gave away the fact that she was teasing, it was fun, lighthearted and free. Dean automatically chuckled, holding his hands out to her in surrender.

“Alright, Sparky,” he joked, moving to place a hold on his hips as he grinned at the woman next to him.

Y/N couldn’t help but feel her stomach jump at the nickname, her mind wandering once again as they held each other’s gaze for a few seconds. She was the one to break it, tucking some hair behind her ears before she looked back out over sea, welcoming the cooling breeze coming in from the ocean.

Noticing the sun's position on the beach, she quickly took a note of the watch on her wrist, the face of the clock telling her it was closing in on three thirty in the afternoon; these past ninety minutes had passed in the blink of an eye. She hadn’t expected the date to be so easy going, or for him to be as he was. She had prepared for a fight, she had prepared for a man who was self serving and wanted just one thing. She had not prepared for Dean Winchester.

She felt quite saddened that she had to wrap this up soon, knowing that her Nanna would need her in an hour or two. Maybe she was making an excuse to leave, because she was overwhelmed and thrown by how different this was to how she had anticipated. Maybe she was trying to play it smart, wanting to finish this on a good note, instead of risking this date turning sour.

“Hey, so there’s a vendor who is famous for his ice cream flavours on the way back home. How about a bowl of creamy goodness to help heal the mighty wound?” She offered, her grin trying to mask her disappointment that she was ending this.

It was almost as if Dean knew that she didn’t want to rush things, that she wanted to leave it on a high as his expression never faltered, his warm eyes full of care and tenderness.

“If we’re talking extra sprinkles, then you’re on.” he winked, after which he reached down to grab his water bottle and shoes with one hand. “Then I’ll walk you to the end of your street.”

The Lieutenant Commander reached out his palm, offering to help her stand. She contemplated his move, wondering whether or not it was the right thing to do. He hadn’t let her down so far, had he? Hesitantly, he took it, her fingers wrapping around his tightly as he assisted her in standing. The feeling that enveloped her was one that she wouldn’t forget easily nor one she wanted too. She was truly captivated by this man and everything he had to offer.

Clearing her throat, she turned in her spot to stoop and collect her things, her shoes and water in one hand, a keen grip on her purse in the other. Dean had already made his way back over to the trees, holding back the branch Y/N had previously, so that she could step through first with no issues. She thanked him, stepping into the clearing before turning to wait for her date to join her.

It was a nice walk back to the harbor, the warm sun on their backs as they made their way to the docks. Both of them disposed their water bottles in a trashcan along the way, the water in them nearly consumed before they stopped to pull their shoes back on their sand covered feet. In the distance, Y/N spotted the ice cream cart that held her favorite cool snack, the vendor behind it being one that she knew, thanks to her many visits to the beach. A quick point of her finger, signalled to Dean that it was the one to head too, both of them hastening their steps, eager for a sweet treat to add to this already sweetened afternoon.

“Hey darlin’. The usual?” The vendor smiled kindly at Y/N as she approached.

His customer nodded her head eagerly, looking forward to the little bowl of chocolate chunk. With a wave, he started on her order before turning to the man that stood beside her. “And you, my friend?”

“Sea salted caramel, please.”

The choice of his ice cream didn’t go unnoticed, and Y/N wondered if he chose sea salted to be clever, considering his occupation, or whether the flavor was actually his favorite. Moving to grab her wallet from her purse, she felt a warm hand on hers to stop her, her eyes catching Dean’s as he shook his head, the vendor already giving him change. 

Dean quickly accepted the two little paper bowls, handing Y/N’s dessert to her before grabbing a napkin, just in case. It was then that they both began to walk, step in step, in the same direction that they had the previous night. The sailor on the same side he was yesterday, only this time dressed in casual clothing and with a spoon full of ice cream in his mouth.

“Guilty pleasure?” the sailor started, earning a perplexed look from the woman next to him which made him chuckle. “The dessert, considering the vendor knows you.”

“Have you tasted it? It’s not that soft serve stuff, this is what ice cream should be, there is nothing I should feel guilty about,” she stated, scooping up some of the chocolatey goodies before guiding it to her mouth, trying her hardest to not let out a little sigh in satisfaction. This was perfect. 

“I must admit, it _is_ good, but--”

“What? Is there a dessert that can beat ice cream?” Y/N cut in, feigning shock as she pulled her paper cup close to her chest. The dessert was her absolute favorite, she would eat it all day long if she could, and if it was healthy enough.

“Hot pecan pie, fresh from the oven,” Dean fired back, without hesitation as he pulled the spoon from his pink lips.

“Hmm,” she pondered in thought, holding the plastic tool in her mouth as she savoured the taste of her treat.

“What?” Dean immediately asked, his eyebrows knitted as he scooped himself some more caramel.

“Bet you often have pie in your mouth, huh?” She couldn’t help the smirk that pulled at her mouth, her counter near enough automatic, her playful eyes peeking to the man next to her to gauge his reaction.

“You're funny, Sparky,” Dean chuckled, his smile beaming as they both broke out in laughter, walking down the sidewalk towards her home.

“I’m hilarious,” she counters, her heart fluttering once more at the nickname he had given her again.

Turning the corner, they both finished their ice cream before arriving at the end of the street. Amused looks coming from both parties as they continued their walk towards Y/N’s home. The sailor let his hands fall loose at his side as he strolled, his fingers brushing hers with each step they made, never intending to take lace them together.

“You know, there was this joke I used to tell my little brother when he was a kid and he would die laughing every time,” Dean told her, a look of glee in his eyes as he waited for her response, his posture relaxed.

“Well don’t leave a girl in suspense,” Y/N coaxed, eager to hear what the Lt. Commander had up his sleeve.

“Alright,” he replied, clearing his throat before a boyish expression took over him, his tongue rolling in his bottom lip. “What do you get when you cross a monkey with dessert?”

A chuckle already passed her lips at the absurdity of it all. “What?”

Dean stopped walking, turning to her before he held his hands up in front of his chest, his fingers pointing as he delivered the punchline. “A meringueutan.” 

Y/N couldn’t help the loud bout of laughter that escaped her, causing passersby to turn in her direction. Automatically, her hand flew to her mouth to try and keep some of the joy in but it was of no use, she was a goner.

“That’s terrible,” she managed to get out, hiccups of humor leaving her. 

“Allowed me to see that smile of yours, though,” he replied softly, the moment becoming gentle all within a few seconds, a blush furiously flooding her cheeks.

It was then that Y/N realised that they had reached the end of her street and that the date was coming to an end. She turned to look at the man in front of her, spinning in her place, the two now mirroring the same positions that they had stood in the night previous.

Dean Winchester was a mystery to her. She had fallen victim of the one liners, the smooth moves and broken promises more than once. She knew all the signs, and yet with the green eyed sailor, something seemed different.

“Thank you, for today,” she breathed, her hands clasping together in front of her.

“You’re welcome,” he replied, honest and true. “I had a good time. I’m hoping that feeling will extend to tomorrow too.”

“You were being serious?” Y/N immediately responded, her brow creasing as she tried to hide the shock that had befallen her face. “You want to dedicate your entire shore leave to this?”

“To _you_ , yes,” Dean smiled, his hands sliding into the front pockets of his jeans. “I still have six days left to prove to you that I’m not an asshole.”

The small chortle that passed her lips was soft and bashful, not really knowing how to feel or react in this moment. Yesterday she was ready to fend him off, her defenses high and her guard in a state of emergency. Yet today, she was curious to find out more about the man who told terrible jokes and liked sea salted ice cream. Part of her was thankful that he had fought for this moment, knowing that she would keep this wonderful day in her memories for a long time to come. The other part, that was still on alert, wondering when the bubble of happiness will pop and allow the wave of reality to crash over her like a tsunami. But light always wins, right?

“I finish at five tomorrow,” came her soft yet simple response, those few words solidifying her next stop on this terrifying journey. 

“Then it’s a date,” he grinned, allowing her to see the natural creases by the corner of his eyes.

She just confirmed his statement with a short nod, not trusting her words at this moment. It was then that she turned, slow steps carrying her to her front door.

“Goodnight ma’am,” Dean called after her, causing her to halt in her tracks. Even after a first date, even after everything he knew, he still hadn’t used her first name, all because she didn’t want him too. She turned to face the charming Lieutenant Commander, a coy smile pulling at her lips as she bit the corner of her lip.

“Call me, Y/N.”


End file.
